2-O-octadecylascorbic acid | 98829-12-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 2-O-octadecylascorbic acid
• 英文别名: 2-O-octadecyl-L-ascorbic acid；(2R)-2-[(1S)-1,2-dihydroxyethyl]-3-hydroxy-4-octadecoxy-2H-furan-5-one
• CAS: 98829-12-0
• 化学式: C₂₄H₄₄O₆
• 分子量: 428.61
• InChiKey: OIRQROBVKNWIIW-RBBKRZOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  30
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  2-O-octadecylascorbic acid 、 乙酰氯 在 吡啶 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以87%的产率得到3-O-acetyl-2-O-octadecylascorbic acid
  参考文献：
  名称：

  Studies on scavengers of active oxygen species. 1. Synthesis and biological activity of 2-O-alkylascorbic acids

  摘要：

  A novel series of 2-O-alkylascorbic acids (5a-u) was synthesized, and their scavenging activities against active oxygen species as well as their suppressive effects on the arrhythmias in rat heart ischemia-reperfusion models were evaluated. Some 2-O-alkylascorbic acids (5e-1) exhibited potent inhibiting activities against lipid peroxidation in rat brain homogenates and in alleviating effects in the ischemia-reperfusion models. Studies on the structure-activity relationship demonstrated that a free 3-enolic hydroxyl group and the longer alkyl chains substituted on the 2-hydroxyl group of ascorbic acid were beneficial for the biological and pharmacological activities. 2-O-Octadecylascorbic acid (5k, CV-3611), one of the most potent and promising compounds, markedly inhibited lipid peroxidation (IC50 = 4.3 X 10(-6) M) and alleviated myocardial lesions induced by ischemia-reperfusion at an oral dose of 1 mg/kg in rats.

  DOI：

  10.1021/jm00399a019
• 作为产物：
  描述：

  5,6-O-isopropylidene-3-O-benzyl-L-ascorbic acid 在 palladium on activated charcoal 盐酸 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二甲基亚砜 为溶剂， 反应 27.0h， 生成 2-O-octadecylascorbic acid
  参考文献：
  名称：

  Studies on scavengers of active oxygen species. 1. Synthesis and biological activity of 2-O-alkylascorbic acids

  摘要：

  A novel series of 2-O-alkylascorbic acids (5a-u) was synthesized, and their scavenging activities against active oxygen species as well as their suppressive effects on the arrhythmias in rat heart ischemia-reperfusion models were evaluated. Some 2-O-alkylascorbic acids (5e-1) exhibited potent inhibiting activities against lipid peroxidation in rat brain homogenates and in alleviating effects in the ischemia-reperfusion models. Studies on the structure-activity relationship demonstrated that a free 3-enolic hydroxyl group and the longer alkyl chains substituted on the 2-hydroxyl group of ascorbic acid were beneficial for the biological and pharmacological activities. 2-O-Octadecylascorbic acid (5k, CV-3611), one of the most potent and promising compounds, markedly inhibited lipid peroxidation (IC50 = 4.3 X 10(-6) M) and alleviated myocardial lesions induced by ischemia-reperfusion at an oral dose of 1 mg/kg in rats.

  DOI：

  10.1021/jm00399a019
• 作为试剂：
  描述：

  2-O-octadecyl-3-O-benzyl-ascorbic acid 在 钯 ethyl acetate diisopropyl ether 、 2-O-octadecylascorbic acid 作用下， 以 乙酸乙酯 为溶剂， 以to give 2-O-octadecylascorbic acid [compound (1-12)](1.5 g)的产率得到2-O-octadecylascorbic acid
  参考文献：
  名称：

  Pharmaceutical compositions containing certain ascorbic acid derivatives

  摘要：

  提供一种抗坏血酸衍生物的公式：##STR1##其中，R.sup.1是具有分子量在15到700之间的有机残基，R.sup.2是氢或羟基，R.sup.3是氢、酰基、可选取代的磷酸酯或磺酸酯，且R.sup.3和羟基或R.sup.2可以形成缩醛残基或缩酮残基，以及其盐。化合物[I]及其盐具有抗氧化活性，对循环功能紊乱具有优异的预防和改善作用，它们可用作食品抗氧化剂和循环功能紊乱预防和改善剂。

  公开号：

  US04959362A1

文献信息

• Ascorbic acid derivatives and their production
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04780549A1

  公开（公告）日：1988-10-25

  An ascorbic acid derivative of the formula: ##STR1## wherein R.sub.1 is an organic residue having a molecular weight of from 58 to 400 is novel compound and is useful as antioxidant agent for food.

  一种化学式为：##STR1## 其中 R.sub.1 是具有分子量从58到400的有机残基的抗坏血酸衍生物是一种新化合物，可用作食品抗氧化剂。
• Conjugates of antioxidants with metal chelating ligands for use in diagnostic and therapeutic allications
  申请人：——

  公开号：US20040082767A1

  公开（公告）日：2004-04-29

  The invention provides radiopharmaceuticals for diagnostic and therapeutic applications, conjugates of antioxidants with metal chelating ligands, intermediate compounds, methods of making such radiopharmaceuticals, ligands, and intermediate compounds, and kits for preparing the radiopharmaceutical complexes.

  本发明提供了用于诊断和治疗应用的放射性药物、抗氧化剂与金属螯合配体的结合物、中间化合物、制备这种放射性药物、配体和中间化合物的方法，以及用于制备放射性药物复合物的试剂盒。
• CONJUGATES OF ANTIOXIDANTS WITH METAL CHELATING LIGANDS FOR USE IN DIAGNOSTIC AND THERAPEUTIC APPLICATIONS
  申请人：Ranganathan S. Ramachandran

  公开号：US20070086944A1

  公开（公告）日：2007-04-19

  The invention provides radiopharmaceuticals for diagnostic and therapeutic applications, conjugates of antioxidants with metal chelating ligands, intermediate compounds, methods of making such radiopharmaceuticals, ligands, and intermediate compounds, and kits for preparing the radiopharmaceutical complexes.

  该发明提供了用于诊断和治疗应用的放射性药物、抗氧化剂与金属螯合配体的结合物、中间化合物、制备这种放射性药物、配体和中间化合物的方法，以及用于制备放射性药物复合物的试剂盒。
• Antiallergic Activity of 3-O-Dodecyl-l-ascorbic Acid
  作者：Takeru Koga、Naoaki Kawahara、Mei Aburada、Asako Ono、Shiori Mae、Aina Yoshida、Yuji Iwaoka、Hideyuki Ito、Akihiro Tai

  DOI：10.3390/molecules29010069

  日期：——

  synthesized, and their degranulation inhibitory activities were evaluated. Among ascorbic acid derivatives with butyl, octyl, dodecyl, hexadecyl, and octadecyl groups introduced at the C-2 or C-3 positions, an AA derivative with a dodecyl group introduced at the C-3 position, 3-O-dodecyl-l-ascorbic acid (compound 8), showed the strongest inhibitory activity against antigen-stimulated degranulation. Compound

  合成了2-O-烷基-L-抗坏血酸和3-O-烷基-L-抗坏血酸，并评价了它们的脱颗粒抑制活性。在C-2或C-3位引入丁基、辛基、十二烷基、十六烷基和十八烷基的抗坏血酸衍生物中，在C-3位引入十二烷基的AA衍生物为3-O-十二烷基-1 -抗坏血酸（化合物8），对抗原刺激的脱颗粒表现出最强的抑制活性。化合物8还抑制钙离子载体刺激的脱颗粒。将化合物8的C-6位的羟基替换为氨基的化合物11和将化合物8的C-3位的十二烷氧基替换为十二烷氨基的化合物12合成的，这些衍生物对抗原刺激的脱粒的抑制活性比化合物8弱。此外，口服化合物8抑制小鼠被动皮肤过敏反应，其效力与抗过敏剂奥沙米特相同。这些结果表明化合物8可能是抗过敏治疗的候选药物。
• Ascorbic acid ethers and their production
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0146121A2

  公开（公告）日：1985-06-26

  An ascorbic acid derivative of the formula: wherein R1 is an organic residue having a molecular weight of from 58 to 400 is novel compound and is useful as antioxidant agent for food.

  式中的抗坏血酸衍生物是一种新型化合物，可用作食品抗氧化剂： 其中 R1 是分子量为 58 至 400 的有机残留物，是一种新型化合物，可用作食品抗氧化剂。